N-(1-phenylhept-2-enyl)-S-(4-methylphenyl)sulfonamide

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: N-(1-phenylhept-2-enyl)-S-(4-methylphenyl)sulfonamide
• 英文别名: 4-methyl-N-[(E)-1-phenylhept-2-enyl]benzenesulfonamide
• 化学式: C₂₀H₂₅NO₂S
• 分子量: 343.49
• InChiKey: IOZJIRHHWQVKHD-FMIVXFBMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  24
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  54.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  N-亚苄基-4-甲基苯磺酰胺 、 1-己炔 在 Schwartz's reagent 、 Dimethylzinc 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 4.16h， 以80%的产率得到N-(1-phenylhept-2-enyl)-S-(4-methylphenyl)sulfonamide
  参考文献：
  名称：

  Dimethylzinc-Mediated Additions of Alkenylzirconocenes to Aldimines. New Methodologies for Allylic Amine and C-Cyclopropylalkylamine Syntheses

  摘要：

  Hydrozirconation of alkynes with zirconocene hydrochloride followed by in situ transmetalation to dimethylzinc provides access to reactive alkenyl organometallic reagents from readily available precursors. Upon addition of imines, 1,2-attack leads to synthetically useful allylic amine building blocks. In the presence of CH2I2 or CH2Cl2, the N-metalated allylic amide intermediate is cyclopropanated and C-cyclopropylalkylamines are formed in high yield and excellent diastereoselectivities favoring the anti products. The use of enynes as starting materials for this domino reaction provides conjugated biscyclopropanes and thus allows the stereoselective formation of five new carbon-carbon bonds. A transition state that explains the need for both zirconocene complex and alkyl zinc in the cyclopropanation reaction is proposed.

  DOI：

  10.1021/ja028092a

文献信息

• Rh(I)-catalyzed addition of alkenylzirconocene chlorides to aldimine derivatives
  作者：Akito Kakuuchi、Takeo Taguchi、Yuji Hanzawa

  DOI：10.1016/s0040-4039(02)02767-3

  日期：2003.1

  of alkenylzirconocene chloride complexes to N-Ts, -PO(OEt)2 and COOR aldimine derivatives were efficiently carried out in dioxane at room temperature to give allylic amine derivatives in excellent yields. This is the first example of the catalytic addition reactions of alkenylzirconocene chloride complexes to aldimine derivatives.

  [RhCl（COD）] 2（2 mol％）在室温下于二恶烷中高效地进行烯基锆茂氯化物与N -Ts，-PO（OEt）2和COOR Aldimine衍生物的催化反应，从而以优异的收率得到烯丙基胺衍生物。这是烯基锆茂金属氯化物配合物与醛亚胺衍生物的催化加成反应的第一个例子。
• Dimethylzinc-Mediated Additions of Alkenylzirconocenes to Aldimines. New Methodologies for Allylic Amine and <i>C</i>-Cyclopropylalkylamine Syntheses
  作者：Peter Wipf、Christopher Kendall、Corey R. J. Stephenson

  DOI：10.1021/ja028092a

  日期：2003.1.1

  Hydrozirconation of alkynes with zirconocene hydrochloride followed by in situ transmetalation to dimethylzinc provides access to reactive alkenyl organometallic reagents from readily available precursors. Upon addition of imines, 1,2-attack leads to synthetically useful allylic amine building blocks. In the presence of CH2I2 or CH2Cl2, the N-metalated allylic amide intermediate is cyclopropanated and C-cyclopropylalkylamines are formed in high yield and excellent diastereoselectivities favoring the anti products. The use of enynes as starting materials for this domino reaction provides conjugated biscyclopropanes and thus allows the stereoselective formation of five new carbon-carbon bonds. A transition state that explains the need for both zirconocene complex and alkyl zinc in the cyclopropanation reaction is proposed.